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| 20.08.1999 | 20:45 | West Bromwich Albion | - | Nottingham Forest | 1:1 (0:0) | |
| 21.08.1999 | 16:00 | Birmingham City | - | Port Vale FC | 4:2 (3:2) | |
| 16:00 | Blackburn Rovers | - | Barnsley FC | 1:2 (0:0) | ||
| 16:00 | Charlton Athletic | - | Norwich City | 1:0 (0:0) | ||
| 16:00 | Crystal Palace | - | Swindon Town | 1:2 (1:1) | ||
| 16:00 | Grimsby Town | - | Fulham FC | 1:1 (1:1) | ||
| 16:00 | Ipswich Town | - | Bolton Wanderers | 1:0 (0:0) | ||
| 16:00 | Manchester City | - | Sheffield United | 6:0 (2:0) | ||
| 16:00 | Portsmouth FC | - | Stockport County | 2:0 (0:0) | ||
| 16:00 | Queens Park Rangers | - | Wolverhampton Wanderers | 1:1 (0:1) | ||
| 16:00 | Tranmere Rovers | - | Huddersfield Town | 1:0 (1:0) | ||
| 16:00 | Walsall FC | - | Crewe Alexandra | 1:4 (1:1) |
| » Classement | équipe recevante | à l'extérieur | Premier tour | Second tour |
| # | Équipe | M. | G. | N. | P. | Buts | Diff. | Pts. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Ipswich Town | 3 | 3 | 0 | 0 | 8:2 | 6 | 9 |
| 2 |
|
Charlton Athletic | 3 | 3 | 0 | 0 | 6:1 | 5 | 9 |
| 3 |
|
Portsmouth FC | 3 | 2 | 1 | 0 | 5:1 | 4 | 7 |
| 4 |
|
Birmingham City | 3 | 2 | 1 | 0 | 7:4 | 3 | 7 |
| 5 |
|
Stockport County | 3 | 2 | 0 | 1 | 3:3 | 0 | 6 |
| 6 |
|
West Bromwich Albion | 3 | 1 | 2 | 0 | 4:3 | 1 | 5 |
| 7 |
|
Wolverhampton Wanderers | 3 | 1 | 2 | 0 | 3:2 | 1 | 5 |
| 8 |
|
Manchester City | 3 | 1 | 1 | 1 | 6:1 | 5 | 4 |
| 9 |
|
Crewe Alexandra | 3 | 1 | 1 | 1 | 5:4 | 1 | 4 |
|
Queens Park Rangers | 3 | 1 | 1 | 1 | 5:4 | 1 | 4 | |
| 11 |
|
Crystal Palace | 3 | 1 | 1 | 1 | 5:5 | 0 | 4 |
| 12 |
|
Bolton Wanderers | 3 | 1 | 1 | 1 | 2:2 | 0 | 4 |
|
Tranmere Rovers | 3 | 1 | 1 | 1 | 2:2 | 0 | 4 | |
| 14 |
|
Nottingham Forest | 3 | 1 | 1 | 1 | 4:5 | -1 | 4 |
| 15 |
|
Swindon Town | 3 | 1 | 1 | 1 | 3:5 | -2 | 4 |
| 16 |
|
Fulham FC | 3 | 0 | 3 | 0 | 3:3 | 0 | 3 |
| 17 |
|
Barnsley FC | 3 | 1 | 0 | 2 | 5:7 | -2 | 3 |
| 18 |
|
Huddersfield Town | 3 | 1 | 0 | 2 | 4:6 | -2 | 3 |
| 19 |
|
Walsall FC | 3 | 0 | 2 | 1 | 2:5 | -3 | 2 |
| 20 |
|
Blackburn Rovers | 3 | 0 | 1 | 2 | 3:5 | -2 | 1 |
| 21 |
|
Grimsby Town | 3 | 0 | 1 | 2 | 2:4 | -2 | 1 |
| 22 |
|
Norwich City | 3 | 0 | 1 | 2 | 1:3 | -2 | 1 |
| 23 |
|
Port Vale FC | 3 | 0 | 1 | 2 | 3:6 | -3 | 1 |
| 24 |
|
Sheffield United | 3 | 0 | 1 | 2 | 1:9 | -8 | 1 |
| Promotion | |
| Relégation |
